Hydrochloric Acid → HCID 86743789, Verbindung

HRID 1587343Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1587343
[CH2:1]([O:3][C:4]([N:6]1[CH2:10][CH2:9][C@@H:8]([CH2:11][CH:12]=O)[C@@H:7]1[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:5])[CH3:2].[Cl-].[CH3:20][O:21]C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CC(C)([O-])C.[K+].O1CCCC1.Cl>O1CCCC1>[CH2:1]([O:3][C:4]([N:6]1[CH2:10][CH2:9][C@@H:8]([CH2:11][CH2:12][CH:20]=[O:21])[C@@H:7]1[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:5])[CH3:2]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 66863523KOtBu THFHCID 86743787trans 1-Ethoxycarbonyl-2-ethoxycarbonylpyrrolidine-3-acetaldehyde

Produkt 1

HCID 86743789HCID 86743789, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To 0.4 g of trans 1-ethoxycarbonyl-2-ethoxycarbonylpyrrolidine-3-acetaldehyde in 5 ml anhydrous tetrahydrofuran under nitrogen, cooled to -78°, is added dropwise a solution of 1.17 g of methoxymethyl-triphenylphosphonium chloride in 15 ml of anhydrous tetrahydrofuran to which is added 1.55 ml of potassium tert-butoxide/tetrahydrofuran (1.6M). Solution is stirred at room temperature for 4 hours. 2N Hydrochloric acid (11 ml) is added and the mixture is stirred for 45 minutes. The solution is concentrated and then extracted with methylene chloride. The extract is dried over sodium sulfate, filtered, concentrated, and the residue is purified by flash chromatography using ethyl acetate/hexane (1:5 to 3:7) to yield trans 1-ethoxycarbonyl-2-ethoxycarbonylpyrrolidine-3-propionaldehyde.

Aufarbeitung

  1. stirringthe mixture is stirred for 45 minutes
  2. concentrationThe solution is concentrated
  3. extractionextracted with methylene chloride
  4. dry with materialThe extract is dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customthe residue is purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-bbff618f2373487fbc31e745729ec0f8
Quelldatensatz
uspto-grants-1993_06
Patentnummer
US05217963

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